99 Oakside Dr, Smithtown, NY 11787
Property image
Property image
OFF MARKET

99 Oakside Dr
Smithtown, NY 11787

  • 3 Beds
  • 2 Baths
  • 2,125 sqft (on 2 acres)

$1,062,300

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $7,101/mo*
Refinance Your Home

$1,062,300

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $7,101/mo*
Refinance Your Home
3 Beds
2 Baths
2,125 sqft
(on 2 acres)

Home Value

Trulia Estimate
$1.06M
Since last month
Increased$1K (+0.1%)
Since last year
Increased$45K (+4.4%)
Since last sale
Increased$496K (+87%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +86% in the last 10 years
MonthEstimated value
2026
August 2026$1.07M
July 2026$1.07M
June 2026$1.07M
May 2026$1.06M
April 2026$1.03M
March 2026$1.03M
February 2026$1.01M
January 2026$1M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1 Valley Avenue, Smithtown, NY
0.21
Single-Family Home
$1,150,000
08/14/26
3
2.5
2,600
4 Burham Court, Smithtown, NY
0.28
Single-Family Home
$950,000
12/22/25
3
2
1,918
1 Clark Street, Smithtown, NY
0.52
Single-Family Home
$850,000
02/20/26
3
2
1,958
158 Landing Meadow Road, Smithtown, NY
0.16
Single-Family Home
$1,495,000
03/12/26
4
3.5
3,634
81 Oakside Road, Smithtown, NY
0.21
Single-Family Home
$450,000
11/06/25
4
2
1,100
56 Rose Street, Smithtown, NY
0.41
Single-Family Home
$680,000
01/22/26
4
2
2,300
368 Landing Avenue, Smithtown, NY
0.51
Single-Family Home
$850,000
03/20/26
4
2.5
2,000
3 Five Acre Court, Smithtown, NY
0.76
Single-Family Home
$950,000
02/17/26
3
2
1,706
24 Ursular Court, Smithtown, NY
0.73
Single-Family Home
$772,000
01/29/26
3
1.5
2,167
17 Thide Court, Smithtown, NY
0.36
Single-Family Home
$1,175,000
04/09/26
5
2.5
3,495

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
445 Landing Avenue, Smithtown, NY 11787
0.09
$854,400
3
1.5
2,500
Off Market
173 Oakside Drive, Smithtown, NY 11787
0.12
$1,027,700
3
2
-
Off Market
467 Landing Avenue, Smithtown, NY 11787
0.14
$842,800
4
2.5
-
Off Market
456 Landing Avenue, Smithtown, NY 11787
0.14
$1,033,800
4
3.5
2,200
Off Market
158 Landing Meadow Road, Smithtown, NY 11787
0.16
$1,495,000
4
3.5
3,634
Recently Sold
109 Oakside Drive, Smithtown, NY 11787
0.18
$1,300,000
4
3.5
2,400
Recently Sold
156 Landing Meadow Road, Smithtown, NY 11787
0.18
$1,056,200
4
3
-
Off Market
83 Oakside Road, Smithtown, NY 11787
0.18
$876,000
4
3
2,103
Off Market
3 Tree Top Terrace, Smithtown, NY 11787
0.20
$1,207,100
4
2.5
3,000
Off Market
410 Landing Avenue, Smithtown, NY 11787
0.21
$819,300
4
2.5
2,433
Off Market
6 Trent Court, Smithtown, NY 11787
0.22
$1,014,400
5
2.5
-
Off Market
1 Valley Avenue, Smithtown, NY 11787
0.21
$1,150,000
3
2.5
2,600
Recently Sold

Local Information

  • Map ViewExplore the area around 99 Oakside Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1959
Lot Size
2 acres
Living Area
2,125 sqft
Price/Sqft
$500

About this House

This Property Offers Privacy And Offers Room For Larger Home Expantion At Later Date.
3 Br 2Fbth L Ranch On Huge 2+Acre Lot .
3 barns (with electric)
inground pool with Large paver patio
Open Floor Plain Hardwood Everywere Vaulted Ceilings,Hi Hats,Granite,Stainless Appliances. Also 3/4 Bsmt 2 Zone Hw Heat,2 Zone Cac. Close To Lirr,Shopping,Restaurants And Much More.
99 Oakside Dr, Smithtown, NY 11787 is a 3 bedroom, 2 bathroom, 2,125 sqft single-family home built in 1959. It last sold for $570,000 on Feb 12, 2015. It is currently off market. The Trulia Estimate is $1,062,300, with a rent estimate of $4,684/month.

Home Details for 99 Oakside Dr

Interior Features

Interior Details
BasementNumber of Rooms: 7Types of Rooms: Breakfast Nook, Dining Room, Family Room, Laundry RoomCeiling Fan
Heating & Cooling
Heating: Baseboard, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or Spa
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Stone, VinylGardenLawnPatioPorchSprinkler System
Pool
Pool
Parking & Garage
Parking: Off Street

Property Information

Year Built
Year Built: 1959Year Updated: 2008
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 2.00 acres

Price and Tax history

DateEventPrice
Feb 12, 2015
Source: OneKey® MLS as distributed by MLS GRID #L2687667
Sold
$570,000
Sep 16, 2014
Source: Agent Provided
ListingRemoved
$599,990
Jul 4, 2014
Source: Agent Provided
Listed For Sale
$599,990
Jan 30, 2013
Source: Agent Provided
ListingRemoved
$550,000
Jun 3, 2012
Source: Agent Provided
Listed For Sale
$550,000

Market trends in Smithtown

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$808K
$4.33KMoM
Sale-to-List Price
—
Price per sq ft
—
Available listings
102
20MoM

Around this home

What Locals Say about Smithtown

At least 232 Trulia users voted on each feature.

  • 92 % Say car is needed

  • 89 % Say it's dog friendly

  • 88 % Say parking is easy

  • 88 % Say yards are well-kept

  • 85 % Say there's holiday spirit

  • 76 % Say it's quiet

  • 74 % Say people would walk alone at night

  • 67 % Say there's wildlife

  • 60 % Say they plan to stay for at least 5 years

  • 60 % Say kids play outside

  • 57 % Say neighbors are friendly

  • 55 % Say streets are well-lit

  • 41 % Say there are sidewalks

  • 39 % Say it's walkable to restaurants

  • 39 % Say there are community events

  • 37 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • nancy hark
    "I have to commute very far - it takes 1-1/2 to 2 hours. There is always traffic on the route. Working from home would be better for me."
    1
    Flag
  • Madeline Barbera
    "There’s a nice dog area in blydenburgh park but this is a horse neighborhood there are over 10,000 horses living here "
    0
    Flag
  • Jackedon24s
    "I’ve lived here my whole life, and everybody is for the most part, friendly and watch out for each other"
    0
    Flag
  • Elle Tee
    "There are lots of families in this area. It’s very neighborly. Only issue would be the occasional larceny out of cars left unlocked at night. "
    2
    Flag
  • Cgallaer
    "Short drive to from the Deer Park and Smithtown LIRR stations. Not too far from the Huntington or Babylon stations. "
    1
    Flag
  • Kimani J.
    "Most residents do not use public transportation. You will need your own vehicle in order to get around. "
    0
    Flag
  • Cgallaer
    "Great place to raise a family with lots of parks and other outdoor activities. It’s also close to other towns in Suffolk County, beaches, and has several LIRR train lines nearby. "
    4
    Flag
  • Cgallaer
    "I work in Manhattan so I take the LIRR to work. There are several train stations in the area and most have lots of parking and good service. "
    3
    Flag
  • Ejclassicdesign
    "Very nice area, safe and close to the beach. Nice school district. It is pricey to attain entrance into the housing market but the values tend to increase relatively fast over time. "
    6
    Flag
  • Robert B.
    "Very safe neighborhood, friendly residents, good schools, very good shopping areas. Has good parks and hiking areas. "
    4
    Flag
  • A &. J. G.
    "Love this neighborhood and having everything so close. I wish there was more Hispanic restaurants around since we love that type of food and have to go far to get it."
    5
    Flag
  • A &. J. G.
    "Quite neighborhood to take a stroll either alone, with the kids or family, or simply to walk the dog. The streets are clean and you feel safe."
    1
    Flag
  • rg9623
    "Smithtown is a great place to raise a family. Has great public schools and has great parks and recreation. Beach’s are close and well maintained "
    5
    Flag
  • Adrian M.
    "Nice houses, safe, close to shopping and entertainment, limited public transportation and expensive."
    0
    Flag
  • hanalu
    "I live here for two years for now, it’s a quiet and safe place, nice people around, and great schools. The tax is crazy high, but if you can handle the housing price and the tax, you are all good to go. Many restaurants nearby, although not very diversity, but still satisfy your basic needs. "
    1
    Flag
  • Laura N.
    "Dog loving community. Great family town. Great school district. Enjoyed 23 years here. Highly recommended."
    0
    Flag
  • Adrian M.
    "The commute itime depends on the time of the day. At noon, traffic can be heavy downtown. Smithtown bypass traffic is usually good."
    0
    Flag
  • Alidalang4
    "Great community and accessibility to shopping and stores . The neighborhoods and neighbor are nice and maintained. Quiet clean neighborhood. "
    1
    Flag
  • Danielle M.
    "Amazing place to raise kids. Great school Districts and opportunities for students to do extra curricular activities as well as sports. The neighborhood is really community oriented and children are often seen in the area playing. One of the biggest benefits is there are many great families and places for the kids to play. I think you will be impressed with the schools and the participation of the staff and teachers. "
    0
    Flag
  • Unspecified
    "Neighbors look out for one another. The homes are well kept. Good schools. Town services are good. Great bars and restaurants nearby."
    1
    Flag
  • Mpyles1982
    "Great schools, early morning drop off available for working parents. A lot of activities to keep your children busy. The only downside is the area lacks diversity."
    0
    Flag
  • Heavensentforeva
    "Great family location. There are also tons of dog people where I currently reside. We usually all walk our dogs together. It is a tight knit community. Everyone pretty much knows everyone on our block. "
    0
    Flag
  • Robertaglasser
    "The homes are very unique many different styles of homes from capes to ranches to split levels nice neighborhoods for raising family "
    1
    Flag
  • Mayivalenzuela
    "We have a very safe, clean and peaceful environment. Near public and private beaches and parks. Great School district. "
    1
    Flag
  • Marissa
    "I’ve lived here for 9 years and everything is centrally located. Wonderful for families especially young ones. "
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 99 Oakside Dr

  • What is 99 Oakside Dr estimated to be worth?
    Trulia's estimated value for 99 Oakside Dr in Smithtown, NY is $1,062,300.
  • What is the price history for 99 Oakside Dr?
    99 Oakside Dr in Smithtown, NY last sold for $570,000 in February 2015.
  • Is Smithtown a buyer's or seller's market?
    Smithtown is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Smithtown?
    The median sale price in Smithtown is $808K. That is up $4.33K from the prior month.
  • Does 99 Oakside Dr have air conditioning?
    Yes, 99 Oakside Dr in Smithtown, NY has air conditioning.
  • Does 99 Oakside Dr have a pool?
    Yes, 99 Oakside Dr in Smithtown, NY has a pool.

Explore by feature - Pet Friendly

6 pet-friendly rentals in Smithtown, NY

Explore by feature - Air Conditioning

9 rentals with air conditioning in Smithtown, NY

Explore by feature - Washer/dryer

8 rentals with a washer/dryer in Smithtown, NY

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Off Market Homes Near 99 Oakside Dr

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